Dibutylamine → HCID 10421590, compound

HRID 412763Notes

Reaction equation

HRID 412763 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH2:10]([NH:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH3:13].CC(C)([O-])C.[Na+]>>[CH2:10]([N:14]([CH2:15][CH2:16][CH2:17][CH3:18])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 3

HCID 8148DibutylamineHCID 121674-ChloroanisoleHCID 23676156Sodium t-butoxide

Product 1

HCID 10421590HCID 10421590, compoundYield 93.1%

Procedure

According to the general procedure B, 4-chloroanisole (150 mg, 1.05 mmol) reacted with N,N-di-n-butylamine (160 mg, 1.24 mmol) using 1 mol % of catalyst and sodium tert-butoxide (120 mg, 1.25 mmol) at 100° C. for 20 h to give the title compound (230 mg, 93%) as an colorless oil: 1H-NMR (400 MHz, CDCl3): δ 6.74 (d, 2H, J=9.2 Hz), 6.58 (d, 2H, J=9.2 Hz), 3.68 (s, 3H), 3.11 (t, 4H, J=8.0 and 7.2 Hz), 1.45 (m, 4H), 1.26 (m, 4H), 0.86 (t, 6H, J=7.6 and 7.2 Hz). 13C{1H}-NMR (100 MHz, CDCl3): δ 150.96, 143.33, 114.79, 114.33, 55.82, 51.65, 29.46, 20.40, 14.02. GC/MS (EI): m/z 235 (M+), 235, 192, 150.

Workup

  1. customat 100° C.
  2. customfor 20 h

Sources & evidence

ORD record
ord-4a98cfa4ea9141408e977584c372b51f
Source dataset
uspto-grants-2003_05
Patent number
US06562989B2

Reaction notes

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